Chicago: Playboy Magazine, 1959. First edition. 5 single sheets. These 5 pages from Hefner, in three letters, dated August 19, 1957--January 31, 1958, and February 26, 1958, reveal a fascinating and illuminating glimpse into the editorial mind of Hugh Hefner directing the efforts of the iconic artist Jack Davis. "Dear Jack, I'd like to do up a finish up for me on the "Take Me To Your Leader" gag. I would like to see another rough on this, however as I see a somewhat different approach taken on it. You can send either a rough or else pencil it on the board and send that before going into a final finish in color." "The old expression, "Take Me To Your Leader," now brings to mind to thousands of "in" people the Martian addressing the cow (or was it a horse?) in The New Yorker Cartoon." "...I would like to see here a very, very far-out jazz musician with thick horn-rimmed glasses and goatee and beret and rather dwarfish stature and long hair, approaching a member of a fairly hip-looking jazz band...", "this gag, as drawn, would have worked out pretty nicely in 1945, when a contrast existed between bop, and Dixieland. But bop is no more. Far better then that we get a contrast between the bop of 10 years ago and the far-out garb that those gents wore, contrasted against the very Ivy and Brooks Brothers cool schoolers of today," And finally, "...our bop musician is just a little too short and monkey-like. If he's extremely weird in stature, it rather destroys the gag, it seems to me. We want to make the most out of the unusual appearance that he maintains through glasses, beard and clothing. If we make him no bigger than a chimpanzee, we fight the gag...let's get him up a bit higher...I want to see him full profile at least, since he's the important bit on this gag." Hef even explains his view of what each musician should look like, down to what they are wearing, even the type of glasses, and how the musical instruments should look, down to the little new hip guy wearing "soft leather shoes". Each of the 3 letters have been signed by Hefner, one a full signature, the other two signed "Hef". Playboy's Head of Readers' Services, Janet Pilgrim, essentially Hef's personal assistant, typed the letters for her boss. And, as any self-respecting Playboy collector knows, Miss Pilgrim was a three-time Playmate and one of the most popular in the magazine's long history. The five pages (three letters) are on Playboy stationery. Along with a copy of the Playboy issue the cartoon ran in on page 59 (the 1959 Jazz All Stars Issue). The letters show some age-toning, but are in overall very good condition. Item #13295